“Open up, big boy.”
Dean holds his mouth wide open as the other man rubs the head of his cock over Dean’s lips.
Now, this isn’t Dean’s usual gig. He’s used to doing some weird stuff for even weirder johns, but that’s mostly jacking them off with his feet or letting them lick his armpits.
He’s grateful he, at least, got to pick the pie flavor.
“That’s it, baby. You like that? Lick it off, don’t be shy.” The man --Gabriel, he said-- orders.
Dean obeys, wrapping his lips around the dick being used to spoon-feed him (...dick-feed him?). The flavor of cherry pie filling explodes in his mouth and, honestly? It’s pretty damn good.
The guy is attractive, but not. Has blond-ish long hair that reminds him a little too much of Sammy, a smile that makes him look like he’s always thinking of something naughty --which wouldn’t surprise Dean--, and his eyes are the color of sunlight shining through a glass of whisky.
But there is something about him, like he’s all over the place and knows exactly what he’s doing at the same time. Like he could sweet-talk you into buying a La-Z-Boy or jumping off a cliff.
Given, he has fucked shadier guys. Like that one time a john asked him to act like a baby, diapers and all. That was a quite… strange experience.
So, he thinks, this dude can’t be too bad. After all, Dean is enjoying himself.
“Now, now, get up, kiddo, on the bed.”
Dean rises from his kneeling position and jumps on the covers, smirking playfully at Gabriel before licking his lips. He finds that he’s not having such a hard time selling this deal.
“On your belly, sweetheart. And no humping the mattress, I don’t want you coming before our time’s up.”
Dean only whines a little, noticing now that he’s hornier than he thought, and lays down.
Gabriel places his hands on the back of Dean’s thighs, kneading with his chubby fingers. “Look at that, baby, such a sweet ass!”
Without any warning, Gabriel bites down on Dean’s right cheek, making him yelp.
“Sorry, kiddo, couldn’t help it.” The man chuckles. “Needed to have a taste.”
Dean feels Gabriel’s thumbs opening him up, exposing his gaping hole to the cool air.
“Figured you’d be ready for this, but looks like you’ll be needing a little more to take me.”
Before Dean knows, a large scoop of pie filling is being spread along the cleft of his ass.
Gabriel doesn’t hesitate to dive right in, pulling a deep groan out of Dean as soon as his tongue makes contact with his entrance.
He licks the filling off, then continues down Dean’s balls and the beginning of his shaft, only teasing for a few seconds and he’s driving Dean crazy.
Dean feels his ass like it’s been sugarcoated, all sticky and kind of uncomfortable, but he finds it hard to care when Gabriel shoves his tongue deeper inside him. The man sure knows how to use it, the long muscle is touching places Dean didn’t even know were worth touching.
Next thing he knows, he’s being manhandled, on his back and legs spread, and Gabriel has a condom on.
“Now, baby boy, I want you to be nice for me and open that pretty mouth of yours.”
Gabriel dips his fingers in cherry pie and offers it to Dean, who doesn’t think twice before sucking Gabriel’s fingers clean.
Dean suppresses a loud moan --this is really good pie--, only to let it out a second later when Gabriel shoves into him.
“Fuck, fuck, fuck!” Gabriel exclaims, starting to thrust right away.
The man fucks him fast and hard, and Dean didn’t imagine such a small man could have hips that strong, but he’s definitely grateful.
Gabriel feeds him more cherry filling again and again, and Dean’s never been so turned on with a john before. He’s hoping Gabriel will call him again sometime, starting to think he could even skip the pay.
No. That’s a no go. He’s doing this for a reason, and it’s not fun. Sammy needs his nerdy books to become a big shot lawyer. Dean shouldn’t let himself get carried away like that again.
Another sharp thrust gets him out of that line of thought, and Dean feels hot all over, and he’s so close, Jesus, he’s gonna explode any time now-
Gabriel beats him to it, shooting into the condom with a long groan, his fingers still in Dean’s mouth.
And Dean can’t take it anymore. He takes Gabriel’s hand and guides it toward his erection, hoping the man won’t be like other asshole johns.
Luckily, Gabriel isn’t, and it only takes a few jerky tugs of his dick to have Dean spilling all over himself. He comes so hard a glub of come lands on his cheekbone, barely missing his eye.
Gabriel falls to his side and whistles, “Whoo! What a ride.”
Dean can’t help but hum in agreement.
Maybe he’s gonna ask for Gabriel’s number. Y’know, in case he gets lonely during his downtime. He sure wouldn’t mind trying this with apple pie next time.